After his split from Bella Hadid in 2019, The Weeknd was most recently linked to DJ Simi Khadra

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The Weeknd is keeping his love life out of the spotlight.

The musician, born Abel Tesfaye, has had his fair share of high-profile romances, but he prefers to keep his dating life private. After being linked to Bella Hadid and Selena Gomez, The Weeknd has reportedly been dating DJ Simi Khadra since 2022.

While discussing his dating life in 2021, he said that he felt “guilty” about bringing attention to the people he dates.

“I try not to do too much. I just try not to bring attention to myself. And I just love being in normal situations, man. It’s such a great feeling. To be able to just like go on a walk and not being in a f—— SUV,” he shared with GQ.

And although he keeps his love life private, The Weeknd has previously said he is looking forward to starting a family.

“I eventually want a family. I know I say I don’t, but I know I do. I want children,” he told GQ. “I feel like having children would influence me and inspire me more.”

Here’s a look at The Weeknd’s dating history.

Bella Hadid

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The Weeknd and the supermodel first connected when he asked her to be on the cover of his 2015 album Beauty Behind the Madness. Although she declined, the musician asked the model to “meet face-to-face.”

Shortly after, they were spotted getting close at Coachella. That summer, the couple were seen on several date nights, including a double date with Hadid’s sister Gigi Hadid and her then-boyfriend Joe Jonas.

In October 2015, the duo celebrated Hadid’s 19th birthday with her family. The Weeknd even gifted the model her own puppy — although he told Rolling Stone that he would probably end up taking care of it. In that same interview, the musician opened up about their relationship for the first time.

“It just kind of fell into my lap,” he told the outlet of dating Hadid. “But if I’d met someone two years ago, I probably would’ve f—— it up. But I’m more — how do I say it? — clear-thinking now.”

Several months later, the couple were still going strong, with Hadid taking a starring role in The Weeknd’s music video for “In the Night.” Despite some breakup rumors, Hadid and The Weeknd made their red carpet debut at the 2016 Grammys, where they posed side by side in matching black outfits. They made several more appearances throughout the year and even attended the Met Gala together.

In the fall of 2016, the couple traveled to Tokyo and celebrated the model’s 20th birthday. Less than a month later, they split after a year and a half of dating. Sources told PEOPLE that it had been difficult to coordinate their schedules, but they still had a “great deal of love for one another and will remain friends.”

Later that month, Hadid proved that the duo were still friendly when she made her Victoria’s Secret Fashion Show debut while The Weeknd performed. Afterward, she told Entertainment Tonight that her ex was “the best and most incredible performer on the planet.”

JAMIE MCCARTHY/FILMMAGIC

Hadid also opened up to Teen Vogue about the breakup, which she said was more difficult than people might have thought. “As an outsider, you might think I handled it so well, but it’s always in your heart, and you always feel it very heavily,” she told the outlet.

“Love hurts, but you have to pull through. But I’ll always respect him, and I’ll always love him. Sometimes you want to be sad about it or handle it differently, but at the end of the day, you never want to burn a bridge that you’ve fought so hard to build,” she added.

In November 2017, a year after their breakup and just weeks after The Weeknd and Gomez broke up, he was spotted stopping by Hadid’s apartment. At the time, sources told PEOPLE the former flames were hanging out again — and the musician had “never stopped loving Bella.”

Their relationship status remained unclear for almost six months, but the duo made headlines again when they were spotted packing on the PDA at Coachella in 2018. Hadid denied kissing her ex at the festival, but just a month later, they were seen sharing a kiss at the Cannes Film Festival. That summer, they teased their relationship on social media but didn’t confirm whether they were dating again. It wasn’t until Hadid’s 22nd birthday in October that the couple made things Instagram official, with Hadid sharing photos embracing The Weeknd at her birthday bash.

Their rekindled romance continued through winter. Hadid gave the musician a shout-out in her Vogue 73 Questions interview, calling him the “most beautiful person” she knew. In February 2019, they celebrated The Weeknd’s 29th birthday in matching camouflage attire.

By that August, however, E! News reported that the pair had split again.

Despite their split, The Weeknd attended Hadid’s 23rd birthday party in October 2019, although sources told PEOPLE that they “just attended as friends.” Not long after, the musician dropped his new song “Heartless,” hinting at his split from Hadid — and when his After Hours album was released in March 2020, fans picked out several other references to the relationship.

Selena Gomez

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The Weeknd reportedly met the “Lose You to Love Me” singer at the 2015 Victoria’s Secret Fashion Show, where they both performed. At the time, The Weeknd was dating Hadid, while Gomez had recently reunited with Justin Bieber. It wasn’t until 2017 that the two artists romantically connected: They were first spotted that January on a romantic dinner date at Giorgio Baldi in Los Angeles.

While sources told PEOPLE the relationship was “new and nothing serious,” things quickly progressed — the couple traveled to Italy just weeks after first being seen together. During their trip abroad, Gomez made their relationship Instagram official, captioning a black-and-white video with a heart eyes emoji.

Following their international getaway, Gomez joined The Weeknd on tour before jetting off to Canada, where the musician showed Gomez his hometown of Toronto. They continued to share their relationship on social media, documenting their weekend at Coachella. Not long after, Gomez later shared why she was so open about her dating life.

“It’s really hard when I would want to spend so much time hiding things. It’s too much pressure, and I think everyone gets over everything eventually … I just want to be happy. If that’s me just being myself, then I don’t really care,” she shared on On Air with Ryan Seacrest.

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The couple made their red carpet debut at the 2017 Met Gala and even got the seal of approval from Gomez’s mom, Mandy Teefey. That summer, The Weeknd continued touring while Gomez underwent a kidney transplant. Despite having to jet around the world on tour, the musician reportedly planned his performances around Gomez’s surgery and recovery to be by her side as much as possible. The Weeknd later alluded to offering her a kidney in his song “Call Out My Name,” in which he wrote, “I almost cut a piece of myself for your life.”

Despite getting cozy on a date in early September 2017, The Weeknd and Gomez went their separate ways just a month later. Sources told PEOPLE that things had been hard for the duo while he was on tour and she was filming in New York City. Gomez later confirmed the breakup, explaining that the split was amicable.

“Something that I’m really proud of is that there’s such a true friendship [between me and The Weeknd],” she told Billboard. “I truly have never experienced anything like that in my life. We ended it as best friends, and it was genuinely about encouraging and caring [for each other], and that was pretty remarkable for me.”

Yovanna Ventura

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In November 2017, The Weeknd was reportedly linked to model Yovanna Ventura. In photos obtained by Just Jared Jr., the pair were spotted leaving a house party in the same car.

Chantel Jeffries

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The Weeknd was briefly linked to model and DJ Chantel Jeffries in April 2018. The Daily Mail obtained photos of the duo sharing some PDA at Coachella. While they looked cozy at the music festival, their fling didn’t appear to extend beyond that weekend.

Angelina Jolie

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In 2021, The Weeknd was rumored to be dating Angelina Jolie after the pair were seen grabbing dinner together in L.A. The duo were spotted together on two occasions, each time dining at celebrity hot spot Giorgio Baldi. Although they left separately after their first dinner together in June, they took the same car to the musician’s Bel Air home in September.

In June, a source told PEOPLE that The Weeknd and Jolie had known each other “for some time” and had bonded over their shared connection to Ethiopia.

Simi Khadra

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The Weeknd was most recently linked to musician Simi Khadra, who is friends with his ex-girlfriend Gomez. The duo sparked dating rumors in early 2022 when they were spotted leaving The Weeknd’s album release party in West Hollywood, California. The following month, they were seen meeting for dinner at Sunset Tower in L.A. Then, just a few weeks later, The Weeknd and Khadra were seen kissing at his 32nd birthday party in Las Vegas.

At the time, sources said The Weeknd was “not in a committed relationship with anyone,” but the rumored couple have since been spotted together several times, including in France ahead of the premiere of The Weeknd’s HBO series The Idol at the 2023 Cannes Film Festival.